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. 2020 Jun 5;22(11):4574-4578.
doi: 10.1021/acs.orglett.0c01705. Epub 2020 May 27.

Rapid Syntheses of [11C]Arylvinyltrifluoromethanes through Treatment of ( E)-Arylvinyl(phenyl)iodonium Tosylates with [11C]Trifluoromethylcopper(I)

Susovan Jana  1 , Sanjay Telu  1 , Bo Yeun Yang  1 , Mohammad B Haskali  1 , Jimmy E Jakobsson  1 , Victor W Pike  1
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Free PMC article

Rapid Syntheses of [11C]Arylvinyltrifluoromethanes through Treatment of ( E)-Arylvinyl(phenyl)iodonium Tosylates with [11C]Trifluoromethylcopper(I)

Susovan Jana et al. Org Lett. .
Free PMC article

Abstract

We report a method for labeling arylvinyltrifluoromethanes with carbon-11 (t1/2 = 20.4 min) as representatives of a new radiolabeled chemotype that has potential for developing radiotracers for biomedical imaging with positron emission tomography. Treatment of (E)-arylvinyl(phenyl)iodonium tosylates (1a-1k) with [11C[CuCF3 gave the corresponding [11C]arylvinyltrifluoromethanes ([11C]2a-[11C]2k) in high radiochemical yields (90-97%) under rapid (2 min) and mild (60 °C) conditions.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1.
Figure 1.
Examples of druglike molecules containing a Cvinyl–CF3 moiety.
Figure 2.
Figure 2.
Methods for constructing the aryl-Cvinyl–CF3 bond.
Figure 3.
Figure 3.
Synthesis of (E)-arylvinyl(phenyl)iodonium tosylates for use as labeling precursors.
Figure 4.
Figure 4.
Synthesis of reference compounds.
Figure 5.
Figure 5.
Reaction scope leading to [11C](E)-arylvinyltrifluoro-methanes. aReaction conditions: 1a–1k (10 μmol), CuBr (5 μmol), KOtBu (15 μmol), Et3N·3HF (5 μmol), DMF (0.7 mL), MeCN (50 μL). [11C]CHF3 was added in DMF solution. bRadio-HPLC yield shown as mean ± SD for n = 3. cIsolated yield shown as mean ± SD for n = 3.
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References

    1. Ametamey SM; Honer M; Schubiger PA Chem. Rev 2008, 108, 1501. - PubMed
    2. Willmann JK; van Bruggen N; Dinkelborg LM; Gambhir SS Nat. Rev. Drug Discovery 2008, 7, 591. - PubMed
    1. Christman DR; Finn RD; Karlstrom KI; Wolf AP Int. J. Appl. Radiat. Isot 1975, 26, 435.
    1. Li Z; Conti PS Adv. Drug Delivery Rev 2010, 62, 1031. - PubMed
    2. Pike VW Curr. Med. Chem 2016, 23, 1818. - PMC - PubMed
    3. Lu S; Siméon FG; Telu S; Cai L; Pike VW The chemistry of labeling heterocycles with carbon-11 or fluorine-18 for biomedical imaging. In Advances in Heterocyclic Chemistry; Scriven EFV, Ramsden CA, Eds.; Academic Press: Cambridge, MA, 2020; Vol. 132, Chapter 4, p 241.
    1. Wuest F; Berndt M; Kniess T. Carbon-11 labeling chemistry based upon [11C]methyl iodide. In PET Chemistry: The Driving Force in Molecular Imaging; Schubiger PA, Lehmann L, Friebe M, Eds.; Springer: New York, 2007; Chapter 7, p183.
    1. Antoni GJ Labelled Compd. Radiopharm 2015, 58, 65. - PubMed

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